


Desperation Day

by Layneee



Category: Supernatural
Genre: Hate Sex, Insult Kink, M/M, Spanking, Speed Dating, Valentine's Day, Well... Dislike Sex, What's the opposite of a praise kink?
Language: English
Status: Completed
Published: 2017-02-14
Updated: 2017-02-14
Packaged: 2018-09-24 05:07:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,309
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9704156
Author URL: https://archiveofourown.org/users/Layneee/pseuds/Layneee
Summary: Much like Valentine's Day itself, Desperation Day dates back thousands of years. Weddings were forbidden under ancient Roman law, so Saint Valentine performed them in secret, under threat of death. And right by Saint Valentine's side was his best bro, Saint Desperatius, there to pick off the insecure.That neediness reaches its climax on February 13. A magical night when a ten has the self-esteem of a four and the depraved enthusiasm of a two. Now, there's only one thing you can't do. Wherever you are, or whoever you're under, you must get home alone by 11:59 p.m.Otherwise, you're on a date on Valentine's Day.





	

"Come on, Dean! This could be so much fun!"

Dean looked at his brother, then down to the flying he so valiantly plucked from the New Seasons bulletin board, then back to his brother, then back to the flyer. 

They flyer in question was large, at least twice the size of his brother's moose paws, and it was in the shape of a heart. It was red, with what looked like a white doily border. The letters looked almost smug, as they proudly proclaimed 'VALENTINE'S DAY SPEED DATING!!!!!' Seriously, who thought it was a good idea to put not one, not two, but five exclamation points?

Sam's face was open and happy, and Dean almost didn't want to break his poor, openminded heart. But he had to. "Hell no." 

"Seriously! It says here," Sam said as he pointed to the fine print, "'All sexualities welcome!'"

"Ugh, dude," Dean said with a grimace and a fake gag. "I can't believe I told you that." 

"Dean! I'm just honored that you trusted me enough to come out," Sam said empathetically. "I'm trying to be supportive."

Dammit. Dean watched as Sam's face transformed to that sad puppy look that works on sorority girls, old ladies and (apparently) older brothers. And Dean supposed that Sam was doing a good job about not being a total chick after learning that Dean swung both ways. 

You gotta throw a puppy a bone sometimes. (Ha!)

"Okay, sheesh! Fine," Dean sighed, only barely hiding his smile when he saw Sam's own return. "I'll go to the stupid singles night."

"It's speed dating, Dean! It's different!" Sam was enthusiastic as he started striding into the store. "How do quinoa bowls sound for dinner? I saw a recipe for tempeh bacon that I'd love to try out."

That stopped Dean in his tracks. Sam, mind only on his creepy health dinner, didn't see. So Dean was forced to yell. "Who the hell are you?" 

Sam spun back around and shushed his brother. "Dude! Shut up. Just let me do this, okay?"

Dean laughed and rolled his eyes. "It's not like I'm going to your stupid speed dating thing, or whatever."

"God, you're annoying. Come on, I'll get the good hipster beer you pretend not to like," Sam said with a roll of his eyes. Then he disappeared behind the organic bread. 

And Dean followed. 

 

XOXOXO

"For the last time, Gabriel, I'm not going to your ridiculous event," Castiel practically growled into his cellphone as he wrote a large 'D' on another students paper in red sharpie. Castiel whipped off his glasses and massaged the bridge of his nose with his free hand. 

Youth is wasted on the young. 

"I have a stack of essays to read and tomorrows lesson to plan." Castiel made a point of picking up another paper and shaking it in his phone's microphone. "See?"

" _Jeez, Sasstiel is back,_ " Gabriel said before pulling a sucker (presumedly,  _hopefully_ ) out of his mouth with a  _pop_. " _Don't want to get laid for Valentine's Day? Or at least get your dick sucked? I'll even get you a room upstairs so you can bone a dude of your choice._ " 

"Must you be so crass?" Castiel took a hearty sip of wine from the glass siting on the coffee table. It was one of his better bottles, a 2013 Burgundy from Domaine des Rouges-Queues Maranges. "I assure you, I'll be fine alone. And it's on the thirteenth, Gabriel. Who throws a holiday event on the day  _before_  the holiday?"

" _Someone booked the space for a wedding day of. Sappy fucks._ " Gabriel sounded jovial because deep,  _deep_ down he was quite the romantic. " _Come on, Cassy! If I can't even get my brother to come the other kids will make fun of me._ "

God, his brother was infantile. And whiny.

"If I go," Castiel conceded with a sigh, making his brother let out a whoop. " _IF_ I go will you allow me to pick the restaurant for my birthday dinner?"

Gabriel whined again. "But I  _always_ pick the restaurant, Cassy!  _God_ , you're such a buzzkill." He sighed. "Fine, whatever. You can pick the restaurant.  _Just this once_."

XOXOXO

Dean figured if he was going to go speed dating, even if it was the day before  _actual_ Valentine's Day, he was going to go all out. So after forcing down the 'dinner' his brother made, he ducked back to the bathroom to shower. He couldn't get all the grease out from under his nails, but he did get clear where it really counted. With a towel wrapped around his waist he went back to his room to change. He pulled out his least destroyed pair of jeans, a charcoal gray button up and a blood red tie. 

Happy fucking Valentine's Day. 

After getting dressed he checked himself out in his full length mirror. From the front to the back, he looked damn faceable, in his own modest opinion. He made sure to grab a travel lube and condom from his bedside table and slip them in his pocket before practically skipping back to the living room. 

Sam was already waiting for him, having just fluffed his hair and changed his shirt. 

"Ready when you are, Sammy," Dean said, slipping his feet into his work boots. Sam wrinkled his nose, but they were the only pair of shoes that Dean's owned. Sue him. 

They drove to the hotel hosting the shindig with nothing but AC/DC blaring through the speakers. There was a spot right in front of the hotel that would solve the ongoing valet issue, so he sped up and around a douchey continental and right into the spot. The continental was obviously not happy with him, if the horn was any indication. Dean just flipped the douche-mobile the bird, and killed the engine. 

"Why are you like this?" Sam asked, face in his hands. 

Dean grinned. "Awesome? I'm just lucky that way." 

Sam shook his head and muttered something not nice under his breath as he pushed open his door. "We gotta register, come on." 

The Elysian Fields Hotel was way too swanky for Dean's taste. They probably offer turndown service and have sheets with more threads than Dean had dollars in his savings account. Sam leads them to a table at the back of the lobby being manned by a man with golden Sam-hair and a snooty looking Indian woman. "Well, well, well. You two here to get down and dirty? Speed style?" He pulled out two hot pink clipboards and handed them across the table. "Hey Cassy! Get a look at Ken doll, here!" The man said to someone over Dean's shoulder. 

"If his car is any indication, I'd say he has a problem with compensation," a deep, thunderstorm voice said snottily. 

"Who the hell are you to talk about my baby like that?" Dean snapped as he spun on his heel, ready to give the arrogant SOB a piece of his mind. Instead he caught sight of dark tousled hair, sea blue eyes, and chapped kissable lips and promptly swallowed his tongue. 

That was one fuckable mouth. 

"Uhh," Dean said smoothly. 

"And he speaks. Can I have my number, Gabriel?" The guy snapped. The guy, Gabriel apparently, handed the hot one a white 'Hello, My Name Is...' sticker with a number '06' on it and two red raffle tickets. 

"Knock 'em dead, big boy," Gabriel said with a wink. The other guy didn't look impressed and simply took his raffle tickets and practically booked it to the bar. 

"You are the best at first impressions, Dean," Sam laughed and Dean punched him on the arm for his sass. 

"Don't worry. Cassy likes 'em sassy." Gabriel picked up a sucker and flicked it at the clipboards still in Sam and Dean's hands. "Once you fill those babies out just give 'em back. The beautiful bisexuals will be the movers, while the glorious gays and straight shooters get a table. Fifteen smackeroonies will get you two drink tickets. Capisce?"

Both brothers nodded and took their florescent clipboards to a set of futuristic looking armchairs in the corner. Sam was still giggling as he sits down, so Dean smacked him on the back of his laughing head with the underside of his clipboard. "Bitch."

Dean practically fell into his seat and looked down at the form. It was pretty standard. Name, age, sex, and address. He'd seen enough Law and Order: SVU to know that the information was crucial in case someone disappeared. Dean wondered why the hell he was thinking that and just filled out his information. Under sexual orientation he almost chickened out and wrote that he was straight, but knew his brother would guilt him for it. So he wrote down 'bisexual' and underlined it for good measure. 

Sam seemed to be all done, so they both went back to the table to get their numbers (Dean got a '02' while Sam got lucky number '13') and their drink tickets. Inside the room was configured so the tables were in a big circle, each decorated with candles, small vases with a single red rose, and gilded cards with loopy numbers. His eyes were drawn to the fourth table, where the hot asshole sat with a large glass of red wine. 

What a douche.

Sam had already gotten a drink and taken his seat, so Dean made his way alone to the bar. 

"What can I gettcha?" The bartender, a pretty brunette with long dark hair and an amazing rack on display in a red halter top, asked him. 

"Double shot of whiskey," Dean told her. She nodded and got his drink quickly. "Thanks," Dean said once he got his drink in hand. The glass was a heavy crystal, and the whiskey surprisingly mediocre. 

The guy from the table appeared suddenly and has somehow acquired a gong, and hit it with (far to close to Dean's ears, thank you very much) a wooden mallet. "Dude!"

"Sorry, kemosabe," Gabriel said with a smirk. "Everyone! Have a seat, and we'll explain the rules."

Dean did as told, if only to save his ears from Gabriel's shrieking. The man at his table was looking at Dean like he was dessert, and it was weirding him out pretty majorly. 

"Okay! So you'll get five minutes at each table. When I bang the gong, what up," he added out of the side of his mouth, "You move on. Other than that just have fun, you horny animals."

He hit the gong again and Dean took that as his cue to start his first 'date.' 

XOXOXO

Dean  _did not_ like his first date. His name was Dick ( _seriously_ ) and Dean suspected that he may actually be a cannibal. Thankfully the gong sounded before Dean had to bypass another joke about how 'tasty' he looked. 

His second date was a lovely woman named Jess, but she was much more Sam's type than Dean's. Dean spent the whole five minutes telling her embarrassing stories about his baby brother, and then slipped her Sam's number when the gong sounded. 

Date number three was a dud, but number four wasn't too bad. Her name was Lisa. She was a yoga teacher and even admitted to having a young son. She had a bright smile and already wouldn't take Dean's shit. But she also spent the majority of the date lamenting about her ex-boyfriend. Dean wasn't opposed to being a rebound, he was normally all for it, but he got the feeling Lisa would feel really guilty afterwards. So when the gong sounded, signaling the end of their date, he gave her a kiss on the back of her hand. "It was a pleasure, Lis."

"Back atcha." Lisa smiled and Dean stood, pulling out the chair for the man after him. The guy grinned, which Dean returned. 

He sat down for his fifth date and looked across the table at the guy Dean had been trying to avoid. 

The hot asshole saw Dean and immediately took a huge gulp of wine. "Hello," he said like it was the worst thing in the world. 

"Hey. I'm Dean." He extended his hand, trying to be the bigger person, but the other guy waited at least twenty seconds before taking it. 

"Castiel." So the guy may be a dick, but there was something about him that lit all of Dean's nerve endings on fire. 

"What do you do, Cas?" Dean was going to try to be nice, if only for the small glimmering hope that he could get this guy into bed. 

"It's  _Castiel_ , and I'm a professor." Okay, so the other guy was kinda an actual asshole. But he still sighed and asked, "You?"

"I'm a mechanic," Dean said. 

And the guy scoffed. He actually scoffed. "Excuse me?"

"I could have guessed that. You reek of oil, and there are stains under your nails. Not to mention that monstrosity of a car. Only someone who thinks things like that matter would drive such a horrendous automobile."

"What the hell's your problem, man?" Dean snapped. "Do you think you're better than me or something?"

Before he could get an answer, Gabriel rang the gong. Dean could see the guy to his right stand up and Dean waved a hand above his head. "Keep movin', buddy. Me and  _Cas_ ain't done yet." 

"Those are not the rules, Dean," Castiel said through gritted teeth. Dean could see that he was white knuckling the stem of his wine glass. 

"You don't know my life, man," Dean said, pointing a menacing finger at the other man's face. Castiel didn't seem phased. "But if you think you know so much about me, go on. I'm fuckin' dying to hear it."

Castiel puffed up like an affronted cat, and downed the rest of his wine. "You think you're better than this. You probably think these people are pathetic for coming to this kind of event."

"Oh please, like you don't think the same," Dean scoffed. "You're here too, buddy. Why's that, huh?"

Castiel sat in silence, sizing Dean up, making Dean feel like he was naked and on display. When the gong signaled again, Castiel very pointedly looked at the next empty chair, but Dean stayed seated. 

There was a woman standing behind Dean, he imagined her arms were crossed and her foot was tapping. But Dean kept his eyes on Castiel. "Empty seat that way. Sorry." Dean said to her, gesturing to the seat on his left. He heard her sigh, but then she moved on. "I'm waiting."

Castiel looked forlornly at his empty wine glass and moved to stand. 

"Nah uh uh, buddy. Sit your ass down," Dean snarled. He snatched up the glass and raised it above his head. If Dean wasn't mistaken, Castiel's eyes lit up with something like intrigue. "Gabe! This douche needs wine." 

Someone snatched the wine from his hand. "Feisty one you got here, bro," Dean heard Gabriel say from behind him. 

"If you must know, you ass, I was blackmailed by my brother. Believe me I had better things to do with my time," Castiel told him. Gabriel appeared, dropping off a full glass of red wine for his brother. 

"What was that? Drink a bottle of shitty wine by yourself?" Dean said with a sarcastic laugh. 

"And what, pray tell, were you're plans?" Castiel took a sip of his wine, looking at Dean over the lip and Dean felt himself get a little stiff. 

Dean realized he was in a delicate spot right now. If he played his cards right, he could turn that little bit of intrigue into a possible rendezvous. Dean always did love rough sex. 

The gong sounded again, but Dean stayed put. "You know the drill," he said to the guy on his right, but the guy didn't seem phased. "My plan was to drink some good whiskey, and have some happy time with myself." Dean leaned forward on his elbows until he felt the heat from the candle warm his face. "Probably with my _dildo_." 

XOXOXO

Castiel had to take a deep breath to calm himself down.

Dean was the most infuriating man Castiel had probably ever met, but he was also build like an adonis. 

On the one hand his brother would needle him for days, possibly weeks if he actually ended up taking this maddening man upstairs. On the other hand, he had a room  _just upstairs_ and he thought Dean deserved to be taught some manners. 

"What? Cat got your tongue?" Dean asked, smirking, as he settled back down on his chair. Castiel could just make out the wide stance of his feet under the table, meaning the man was spreading his legs invitingly. Castiel slipped his foot up silently and pressed it threateningly over Dean's crotch. 

Dean was half hard and getting harder. 

"Listen her you insolent child," Castiel growled. He watched as Dean's pupils dilated. "You are a brat, and you're loud. But I have a room upstairs and I would really love to fuck some of that rudeness out of you. Are you amenable to that, Dean?" 

Dean swallowed visibly, and his cock twitched so hard Castiel could feel it under his shoe. 

"Uhh," Dean stammered. Only this time it was almost charming. "Yeah, I'd find that  _amenable_." 

Castiel knew Dean was making fun of him, but he couldn't find the will to care. The gong rang again and both men stood. The whole room honest to God applauded. Castiel shot the room a glare and they quieted. "Move," he hissed and Dean did. Silently they made their way to the elevator. Once inside Castiel hit the button for the fifth floor. Once the doors were shut he let himself move into Dean's space. 

Dean allowed himself to be corralled into the corner of the elevator, and when Castiel pried his lips open with his tongue, Dean just moaned and opened beautifully. He tasted like the whiskey he'd been drinking, and his hands stayed clutched at the railing behind them. 

"You're such an asshole," Dean moaned as soon as Castiel pulled away. 

"Watch your tongue." Castiel moved his fingers into Dean's mouth, pressing down on said wicked tongue. Dean took it a step further and began to suck. "Groveling won't make me go easy on you."

Dean pushed at Castiel's fingers with his deft tongue until they slipped past his lips and smirked. "Good."

When the doors opened Castiel practically dragged Dean to the room Gabriel got him. Once they were past the threshold Castiel pushed Dean backwards with enough force that the other man stumbled over his own feel and fell ass first on the mattress. 

It was a king, because apparently Gabriel didn't skimp when helping his brother have sex.

Dean looked up at him in aww as Castiel slowly slipped his blazer off his shoulders and took off his tie. Once Castiel was down to just his white button up he rolled the sleeves up to his elbow. 

"My turn," Dean said. He stood, bringing them chest to chest and kissed Castiel. It was immediately deep and dirty. Castiel almost didn't feel Dean turn them until Castiel felt the bed behind his knees. "Sit."

Castiel did. 

Dean took a step back, looking smug. He stripped off his clothes slowly, but without much fanfare. Once he was completely bare he stayed standing just out of reach, giving Castiel an opportunity to look his fill. Dean was a beautiful specimen. His shoulders were broad, and his arms were build in a way that made Castiel take back everything he had ever said about mechanics. He was a little soft around the middle, but it was endearing. His legs were bowed, perfect for Castiel to slide between. And his cock. It was hard, and flushed red with arousal. Perfect, pearly beads of precome were already leaking out of the slit. 

"Not overcompensating now, am I?" Dean asked as he gripped his cock in his own hand and stroked. 

Castiel raised a brow. 

This insolent man was going to be the end of him. 

Castiel crooked a finger at Dean, signaling him to get closer, then patted his lap. Dean got the hint and crawled into Castiel's lap, straddling his thighs. 

Their lips met again like two comets. Dean gyrated on his lap like a deprived stripper. Castiel could feel Dean's cock leaking against his stomach, soaking through his button up. 

Again, as if reading his mind, Dean began to unbutton the white, starched cotton. "So hot, Cas."

" _Castiel_ ," Cas moaned, realizing how weird it was to moan his own name. They kissed, tongues battling for dominance, a battle that Dean would ultimately loose. 

When Castiel pulled away he was panting, and felt like his cock was about to bust through his slacks. "Get on your hands and knees."

Dean scrambled to comply. But once he did, it was a beautiful sight. Castiel didn't waste any time waiting to get his hands back on Dean. Using his hands he spread Dean's cheek and rubbed both thumbs over his hole. It was perfectly pink and crinkled. Just waiting for Castiel to fill it. 

Castiel placed a kiss on each kiss and then dived right in. Tongue first. 

The sounds escaping Dean's lips as Castiel ate him out were loud and deep. It also only took a moment until Castiel realized that Dean felt looser than he should be. He pulled back, making Dean whine. Castiel immediately replaced his tongue with a finger. "Did you already finger yourself, Dean?"

Dean moaned as Castiel was able to zero in on Dean's prostate. He nodded his head, and Castiel rolled his eyes. 

"You're so presumptuous. Coming here, expecting your charms to do all the work and get you into some poor strangers bed." Castiel really wanted to add a second finger, but knew he couldn't without lube. "I'm assuming you brought lubricant?"

"In my...  _nngh_ ," Dean broke off with a moan. "Jeans."

"Get a finger wet for me, Dean." Not a second later Castiel watched as Dean put one of his own fingers into his mouth. Castiel swirled his finger as he waited for Dean to deem the fingers wet enough. Once Dean offered his hand back, Castiel pulled his hand free and replaced it with Dean's. "Keep that there."

Castiel went back to Dean's stack of clothes, finding the lube and condoms almost immediately. He took the break to strip completely and roll the condom on. He kneed his way back towards Dean on the bed, and smacked Dean's hand away from his hole. Castiel lubed up his fingers and dove right back in. 

There were no words spoken, only moans filling the room as Castiel loosened Dean.

"I'm fucking ready, man, jeez," Dean groaned. 

"So you're impatient, too," Castiel commented. "Doesn't surprise me."

"Asshole," Dean swore. 

Then, before Castiel knew what was happening, Dean was manhandling Castiel onto his back and sinking down on Castiel's cock. 

"Oh fuck," Castiel gasped. 

"Ha!" Dean laughed, squeezing his muscles just so to make Castiel buck up. "It's hilarious hearing you swear. You pretentious son of a bitch."

"I'm not pretentious," Castiel said. He gripped Dean by his hips and thrusted. 

"Yeah right,  _professor_ ," Dean replied with a grin. He was moving on top of Castiel like a professional. Little breathy moans were spilling from his mouth, and his thumbs were absentmindedly stroking Castiel's nipples. 

Castiel couldn't help but grin. "Technically I'm a doctor."

" _So_ pretentious." Dean actually laughed. "Now stop talking."

All bets were off. Dean started riding Castiel hard. Pulling nearly all the way off then slamming back down. Castiel could feel himself getting close, and moved to get his hands on Dean's erection, but his hand was slapped away. 

"Not yet. Wanna keep doing this," Dean moaned. "You better not come yet." 

Castiel pulled Dean down into a kiss, bending him forward enough to expose more of his ass. Then he spanked that perky ass. "Don't be rude." 

Dean pushed back against Castiel's hand. "Do that again."

Part of Castiel wanted to wait, really make Dean beg, but the idea of turning Dean's ass bright red was appealing. So he pulled his hand back and brought it down, right where his first smack landed. He did this again, and again. Until Dean was shaking on top of him, panting into Castiel's mouth. 

Once Castiel felt that Dean had had enough he pushed him upright before rolling on top of the other man. 

He felt himself loosing control as he thrust into Dean's wet heat. 

Dean was screaming, passion making his eyes squeeze shut. "How can you be such a frigid asshole, but fuck me so good?" Dean managed to ask, between breaths. 

"I'm not frigid," Castiel said as he grabbed Dean's ankles, wrapping one around his waist and the other above his shoulder. "I just appreciate being succinct."

Dean couldn't respond, as the new position was nailing his prostate. Castiel grinned. "Cat got your tongue?"

Dean's face scrunched up like he wanted to fight back, but at that moment he came, unexpectedly. Castiel watched, enthralled, as Dean fell apart underneath him. His face was slack in pleasure and Castiel wished he had some artistic talent so he could capture it. As Dean came down from the aftershocks his body was convulsing, squeezing Castiel's cock. 

Then he was coming as well, filling the condom as he fell forward and right into Dean's waiting lips. Castiel pulled out of Dean's spent body and collapsed into the mattress.  

They sat in the dark, quietly, until Dean caught sight of something on Castiel's other side. 

He started to laugh. 

Castiel turned his head and saw the clock. It read 12:01 in bright red letters. Castiel turned back to Dean, who was smiling. "Happy Valentine's Day, asshole."

**Author's Note:**

> Happy Valentine's Day, you filthy creatures. 
> 
> XOXO


End file.
